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Hickey and Squaw Loop is a 2.8 mile heavily trafficked loop trail located near Stockbridge, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

Length 2.8 mi Elevation gain 685 ft Route type Loop

Dogs on leash

Kid friendly

Camping

Cross country skiing

Hiking

Nature trips

Snowshoeing

Bird watching

Running

Forest

Views

Wild flowers

Wildlife

Rocky

Scramble

Description
Waypoints (0)

Note: The term squaw is considered universally offensive by Indigenous groups in America due to its use for hundreds of years in a derogatory context. Indigenous activists have continued to work both locally and in more general educational efforts, to rename the locations across North America that contain the slur, as well as to eliminate the slur from the lexicon in general. See here for more info: https://en.wikipedia.org/wiki/Squaw#Efforts_to_rename_placenames_and_terms_with_squaw_in_them

Weather
UV Index
Daylight
Reviews (438)
Photos (258)
Recordings (330)
Completed (825)
Anna Peditto
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HikingScramble

Moderate trail with amazing views! The trail itself was beautiful but was a bit more crowded than I’d prefer. Overall loved the hike and the amazing staff.

Kevin Ryan
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HikingRockyScramble

Consider taking a short detour to devils pulpit overlook. It will take 5 minutes just off of the squaw trail and worth it for the beautiful vista

View Kevin's Recording
Anthony Jillions
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Hiking

Great trail didn’t go up Devils Pulpit but ranger said there are currently 4 peregrine falcons up there

View Anthony's Recording
Carol Alaimo
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HikingFeeGreat!Rocky

We've hiked Monument a few times during different seasons. It's always a great hike!

Alli Fish
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Hiking

Amazing hike! We took our 3 boys ages 8, 7, and 5. They loved it!

Katharine Curtis
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HikingBugs
View Katharine's Recording
Joe McCarthy
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Awesome hike. You have 3 different hikes in 1.

View Joe's Recording
Lyssa Manning
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Hiking

Awesome short hike. Great views, helpful volunteer, not too packed and most people respectful about wearing masks as you pass

Samantha Levin
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HikingBugsRockyScramble

The trail was beautiful and not too many people there when we went. There were some great places to take pictures and have a little rest when needed. There are some rocks and roots throughout so make sure you’re wearing solid shoes! Enjoy!

View Samantha's Recording
Elizabeth Radcliffe
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HikingRockyScramble

This was a fantastic hike for our kids 6, 9 and 11. Definitely a workout and some rock scrambling but great moderate hike for kids with incredible views. Our kids’ first real experience with a “payoff” hike. Mostly shade and interesting rock formations throughout.

View Elizabeth's Recording
Megan Cassidy
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HikingFeeMuddy

Great views! A little muddy in some spots. There is a $5 parking fee.

Ryan Aeschlimann
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HikingRocky
View Ryan's Recording
Amanda Mulligan
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Hiking

The trails were open today, great views from devils palpate and the summit. Invigorating hike up using hickey to squaw then a relaxing stroll around the mountain via Indian trail. Overall, amazing hike. No fee, pay station was closed and bonus, no bugs when we were there.

H B
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Hiking

Outstanding, 360 degree views for relatively little effort.

James Ader
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closed

Steven Anderson
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HikingSnow

This is my go to training mountain. Hike it 2 times a month and a good work out going up the steep hickey trail. Like the view of greylock on a clear day. I do this in addition to other training. Frequent Taft farms after the climb. I do his year round and love the snow hikes when available. Have fun!

View Steven's Recording
Olga Kim
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Hiking

My favorite trail of all time. Beautiful views- make sure to climb the stone steps to devils pulpit overlook. That is my favorite view. The only downside is that it’s a top hiking spot and can be swamped with people during the summer and weekends.

Amanda Bowman
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Hiking

Do well maintained! Beautiful.

View Amanda's Recording
Jami Ricard
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HikingIcy
View Jami's Recording
Mike Wilkos
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HikingScramble
View Mike's Recording
Michael Langer
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Hiking

Great hike at a relaxed pace, took about 75 minutes! Lost the trail a couple times, but that led to a great lookout. Definitely recommend.

Horn Coyle
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Hiking

Great views!!

Rose Hooten
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Hiking

Hard to see the trail with all the fallen leaves, but overall beautiful with a few nice viewpoints.

View Rose's Recording
Showing results 1 - 23 of 438